DE1570398B2 - - Google Patents
Info
- Publication number
- DE1570398B2 DE1570398B2 DE1570398A DE1570398A DE1570398B2 DE 1570398 B2 DE1570398 B2 DE 1570398B2 DE 1570398 A DE1570398 A DE 1570398A DE 1570398 A DE1570398 A DE 1570398A DE 1570398 B2 DE1570398 B2 DE 1570398B2
- Authority
- DE
- Germany
- Prior art keywords
- mol
- alcoholic solution
- kernhalogeniertem
- polymerization catalyst
- monobromoethylbenzene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 claims description 12
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical class BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 claims description 11
- 230000001476 alcoholic effect Effects 0.000 claims description 10
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002685 polymerization catalyst Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 4
- -1 divinyl compound Chemical class 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000003440 styrenes Chemical class 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000007269 dehydrobromination reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WMUQCGDDDFBZAR-UHFFFAOYSA-N 1,3,5-tribromo-2-(2-bromoethyl)benzene Chemical compound BrCCC1=C(Br)C=C(Br)C=C1Br WMUQCGDDDFBZAR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/16—Halogens
- C08F212/21—Bromine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
- C08F212/36—Divinylbenzene
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511570398 DE1570398A1 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur Herstellung von vernetzten,kernhalogeniertes Styrol enthaltenden Copolymerisaten |
| DE19651570395 DE1570395B1 (de) | 1951-01-28 | 1965-10-16 | Verfahren zur Herstellung von kernhalogeniertem Polystyrol |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511570398 DE1570398A1 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur Herstellung von vernetzten,kernhalogeniertes Styrol enthaltenden Copolymerisaten |
| DEC0037182 | 1965-10-16 | ||
| DEC0037297 | 1965-11-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1570398A1 DE1570398A1 (de) | 1969-09-04 |
| DE1570398B2 true DE1570398B2 (enrdf_load_stackoverflow) | 1973-10-18 |
| DE1570398C3 DE1570398C3 (enrdf_load_stackoverflow) | 1974-05-30 |
Family
ID=27180822
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19511570398 Granted DE1570398A1 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur Herstellung von vernetzten,kernhalogeniertes Styrol enthaltenden Copolymerisaten |
| DE19651570395 Ceased DE1570395B1 (de) | 1951-01-28 | 1965-10-16 | Verfahren zur Herstellung von kernhalogeniertem Polystyrol |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651570395 Ceased DE1570395B1 (de) | 1951-01-28 | 1965-10-16 | Verfahren zur Herstellung von kernhalogeniertem Polystyrol |
Country Status (1)
| Country | Link |
|---|---|
| DE (2) | DE1570398A1 (enrdf_load_stackoverflow) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH584731A5 (enrdf_load_stackoverflow) * | 1973-12-17 | 1977-02-15 | Ciba Geigy Ag | |
| JPS51105389A (en) * | 1975-03-01 | 1976-09-17 | Kenji Kanezaki | Kojundo pp binirufuenoorujugotaino seizohoho |
| DE2800012B2 (de) * | 1978-01-02 | 1981-08-13 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von wärmebeständigen, kernbromierten Polystyrolen |
| DE3025666C2 (de) * | 1980-07-07 | 1983-01-20 | Chemische Fabrik Kalk GmbH, 5000 Köln | Polymeres Pentabromstyrol, Verfahren zur Herstellung und Verwendung |
| US4755573A (en) * | 1985-11-15 | 1988-07-05 | General Electric Company | Cationic polymerization of bromoalkenyl aromatic compounds with aromatic chain transfer agent, and products |
| IL79499A0 (en) * | 1986-07-23 | 1986-10-31 | Yeda Res & Dev | Production of crystalline tribromostyrene |
| KR100332859B1 (ko) * | 1993-07-28 | 2002-11-23 | 롬 앤드 하스 캄파니 | 밀도가높고,표면적이넓은흡착제 |
| US20050159552A1 (en) | 2004-01-21 | 2005-07-21 | Reed Jon S. | Flame retarded fibers and filaments and process of production therefor |
| US7666944B2 (en) | 2004-01-21 | 2010-02-23 | Albemarle Corporation | Flame retarded fibers and filaments and process of production therefor |
-
1951
- 1951-01-28 DE DE19511570398 patent/DE1570398A1/de active Granted
-
1965
- 1965-10-16 DE DE19651570395 patent/DE1570395B1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE1570398C3 (enrdf_load_stackoverflow) | 1974-05-30 |
| DE1570395B1 (de) | 1969-11-13 |
| DE1570398A1 (de) | 1969-09-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |